Company Description

Gatehouse Design and Developments specializes in designing and building high-quality homes with a focus on craftsmanship and attention to detail. Dedicated to enhancing how people live, the team prioritizes thoughtful planning and livability in every project, ensuring a seamless homeowner experience. By collaborating with highly skilled professionals, Gatehouse upholds a strong commitment to quality and precision. Every project reflects pride in workmanship and a passion for creating homes that embody character and meaning. The team’s values are grounded in respect, skill, and a mission to elevate industry standards.

About the Role

We’re looking for a highly capable, innovative Executive Assistant who will serve as a true partner to the CFO—not just maintain systems, but add value, improve processes, and think strategically about how finance and operations support our growth.

This role blends high-level executive support with hands-on finance operations (AR/AP, QuickBooks Online, project tracking) plus light legal/transactional coordination across multiple entities and joint ventures. You’ll work in-office and be deeply embedded in the day‑to‑day engine of the business.

This is ideal for someone who:

Understands the big picture behind the numbers and structures.
Enjoys building and improving systems, not just following them.
Likes working with multiple entities, org charts, and deal structures in a fast-moving real estate environment.

Key Responsibilities

Executive Support to the CFO

Manage the CFO’s calendar, meetings, and priorities across multiple projects, entities, and partners.
Organize and prepare materials for lender, investor, and internal finance meetings (agendas, financial summaries, supporting documents).
Draft, edit, and organize emails and correspondence on behalf of the CFO, maintaining a professional tone with lenders, investors, attorneys, and partners.
Anticipate information and support needs—proactively surface issues, deadlines, and opportunities for improvement.

Finance & Project Support

Handle day-to-day finance tasks, including:
End-to-end AR/AP management (5+ years’ experience): vendor invoices, payment runs, aging reports, and reconciliations.
Entering and maintaining clean books in QuickBooks Online (2+ years’ hands-on experience required).
Coordinating with external accountants/bookkeepers to ensure accuracy and completeness.
Assist with monthly/quarterly reporting packages for projects and corporate entities.
Track key financial dates and obligations: loan draws, interest payments, tax deadlines, lender and investor reporting.
Maintain organized digital folders and filing systems for financial statements, loan documents, development budgets, and draw packages.
Use advanced Excel skills (pivot tables, lookups, formulas) to build and maintain trackers, reconciliations, and reports.

Legal, Entity & Transactional Coordination (Asset Skill)

Support coordination of transaction documents for acquisitions, financings, and dispositions (PSAs, loan agreements, easements, leases) in collaboration with outside counsel.
Maintain and organize corporate/entity records: LLCs, operating agreements, resolutions, signature pages, etc.
Assist with incorporation and entity setup across multiple organizations, including maintaining org charts and entity structures.
Understand and help track different company setups, including joint venture agreements and partner structures (not providing legal advice, but understanding the mechanics and documentation).
Track critical dates (closing dates, contingencies, option periods, renewal options, notice deadlines) and surface them to the CFO in advance.
Review basic documents for completeness and consistency and coordinate revisions with attorneys, counterparties, and internal stakeholders.

Process, Systems, AI & Optimization

Build and refine checklists, trackers, templates, and SOPs for:
Closings and loan draw processes.
Quarterly reporting and recurring finance tasks.
Document management, approvals, and signature workflows.
Leverage AI tools (e.g., ChatGPT/Copilot-type tools) to:
Draft emails, summaries, and standardized documents.
Help analyze data, detect inconsistencies, and improve reporting.
Streamline repetitive tasks and improve overall productivity.
Continuously look for ways to improve and modernize systems, reduce friction, and speed up information flow to and from the CFO.
Monitor outstanding tasks and follow-ups, making sure projects and obligations move forward on schedule.

Cross-Functional & Stakeholder Coordination

Coordinate with internal teams (development, construction, property management, accounting) to gather information needed by the CFO.
Serve as a professional, responsive point of contact for lenders, investors, partners, and legal counsel seeking information from the CFO.
Handle sensitive and confidential information with discretion and sound judgment.

Required Qualifications

5+ years of experience in a finance/operations support role such as Executive Assistant to a senior finance leader, Operations Coordinator, or similar.
Minimum 5 years of hands-on AR/AP experience, including managing invoice workflows, payment runs, and reconciliations.
Minimum 2 years of hands-on experience with QuickBooks Online (not just desktop) including multi-entity setups, classes, and project/department coding.
5+ years of Microsoft Office Suite experience with advanced skills in Excel and Word (complex formulas, pivot tables, formatting, mail merges, templates).
Demonstrated experience working with multiple entities, org charts, and incorporation processes.
Understanding of different company setups, including joint ventures and partnerships, and how they show up in documents and basic financials.
High attention to detail, with a track record of low error rates in financial and legal/transactional documents.
Comfort using and learning AI tools and technology platforms to improve workflows and productivity.
Excellent written and verbal communication skills; able to communicate clearly and professionally with external stakeholders.

Preferred / Asset Experience

Experience in real estate, construction, or development (strong plus).
Banking and/or paralegal/legal assistant experience—especially in real estate, corporate, or transactional law—is a significant asset.
Working knowledge of basic accounting and finance concepts beyond AR/AP (general ledger, project-based financials, budgets, soft vs. hard costs).
Experience with other accounting or project management tools (e.g., Yardi, Procore, or similar) is a plus.
Bachelor’s degree in Business, Finance, Real Estate, or related field preferred (or equivalent experience).

Personal Traits & Working Style

We’re looking for someone who:

Brings a proactive, “value-add” mindset—anticipates needs and suggests improvements instead of waiting for direction.
Understands the bigger picture of how finance, entities, and deals fit together—and enjoys learning more about it.
Is extremely organized and detail-focused, comfortable managing many moving parts across multiple projects and entities.
Enjoys structure, systems, and optimization—likes building better processes and keeping everything neat and trackable.
Thrives in a fast-paced, deadline-driven environment typical of real estate closings, loan draws, and development milestones.
Has a high sense of urgency and follow-through, keeping tasks moving until they’re fully completed.
Is comfortable working with both numbers and documents—spreadsheets, financial reports, contracts, and closing binders.
Operates with discretion, integrity, and professionalism at all times.

Please email cover letter and resume to jeff@madebygatehouse.com

Gatehouse Design And Developments Jobs

Executive Assistant to Chief Financial Officer